Cherelle Parker made history as the first woman elected Philly mayor. Now comes the hard part.

The contrast was stark.

There, on the wall of the Mayor’s Reception Room in Philadelphia’s iconic City Hall, were lines of oil paintings of mayors past. They wore dark suits and ties with their dusty wigs and long beards.

And standing beneath them last week in a bright orange pantsuit was Mayor-elect Cherelle Parker, the 100th leader to join their exclusive club, commanding a room of advisers, bantering with supporters, and vowing to a downtrodden city that she will restore its “hope deficit.”

Parker’s elevation to become the first woman in history to serve as mayor of America’s sixth-largest city and the birthplace of democracy has been, for many, a long time coming. It’s been described as an inspirational moment for Black women, in particular, who finally see themselves represented in the city’s highest office.

But while Parker navigates a host of generational challenges afflicting the city, she’ll also have to overcome unique obstacles that only women face, and those will be compounded because she is Black, according to interviews with more than a dozen women who are mayors, CEOs, and leadership experts. They said Parker will be held to higher standards, judged more harshly, and subjected to stereotypes her predecessors never were.

She’ll have to grapple with what social scientists call the double bias: Women in leadership are expected to act one way, but if they act the way they’re expected to, then they are not seen as a leader — because we expect leaders to act like men.

“Women are judged differently. Black women are judged even harsher,” said Stephanie Rawlings-Blake, the former mayor of Baltimore. “If you’re serious, people think that you’re unhappy. If you’re focusing on the work, you’re not relatable.”

And then, among a staff of dozens and a workforce of roughly 25,000, there will be people who are simply uncomfortable with a woman at the helm. Some will say so. Others may say they just don’t like her, but can’t quite put their finger on why.

Those who know Parker best say her decades of experience in politics prepared her to enter the job clear-eyed about what she’ll face.

“She doesn’t look like the other 99 men, and so she is going to have unfair presumptions about her,” said Della Clark, president of the Enterprise Center and cochair of Parker’s transition committee. “But I know she has the personality to overcome it. She is strong-willed, and feels that everything in her life has prepared her for this role.”

Parker’s staff saw bias through the campaign. Senior adviser Aren Platt, who led Parker’s fundraising effort, said the campaign struggled to raise money, especially early on, because potential donors were skeptical of her viability.

”She is unquestionably qualified. She has a brilliance to her,” he said. “But for Cherelle — and I’m only left to assume that this is because she’s a Black woman — she needed to qualify herself [to donors] to run for mayor again and again and again.”

And it’s played out recently for other women in both local and national politics.

Vice President Kamala Harris, the first woman to hold that job, has one of the lowest approval ratings of any vice president in modern history, and research shows she’s faced a staggering volume of online abuse. Former Philadelphia Police Commissioner Danielle Outlaw was the first Black woman to lead the force, and was at times ridiculed for her appearance or style of speaking.

Former Chicago Mayor Lori Lightfoot, the first Black woman and openly LGBTQ head of the city, told the New York Times at the end of her tenure: “I’m always going to be viewed through a different lens, that the things I do and say, that the toughness that I exhibit, is viewed as divisive, that I’m the mean mayor, that I can’t collaborate with anyone.”

Women in leadership said the prejudices can play out in small ways. Harrisburg Mayor Wanda Williams, a Democrat and former president of the city council, said that sometimes constituents or colleagues address her by her first name, something she said they may be more comfortable doing because she’s a woman.

“I remind them that I’m Mayor Wanda Williams, and you identify me as such,” she said. “The position demands respect.”

» READ MORE: Cherelle Parker shattered a glass ceiling, but Black female mayors still face racial and gender bias

Terri Boyer, director of Villanova’s McNulty Institute for Women’s Leadership, said women still make up less than a third of big-city mayors. Because of that reality, coupled with Parker being Philadelphia’s first female mayor, Boyer said she faces what experts call “the glass cliff scenario.”

The idea, Boyer said, is that a woman may have broken a glass ceiling, but conditions were set up for her to fail.

“That hyper-scrutiny that she’s going to have as the first Black woman in the role means that people are going to be watching everything,” Boyer said. “It means she might go in there and people will be like, ‘We put a woman in there, and she fell off the cliff.’”

Leslie Richards, now the general manager of SEPTA, was in 2015 the first woman to serve as secretary of the state Department of Transportation. She said she felt a freedom to be herself and to chart a new direction for the agency, because no matter what she did, it was seen as unexpected.

But she said she felt daily pressures associated with being the first.

“I even promised Gov. Wolf that I was going to give the job everything so that he wouldn’t be looked at as the governor who gave a female a shot at that position and it didn’t work out,” she said. “I felt that pressure with everything that I did.”

Richards said that when she drove around the state in her government-issued car, she would pray she wouldn’t get into a fender bender, “because then I would be known as the female PennDot secretary who crashed the state car.”

She never got a scratch on it.

Madeline Bell, president and CEO of Children’s Hospital of Philadelphia and one of the only female chief executives in the region, said it was Parker who recently gave her some advice — though the next mayor might not have known it.

Bell attended a talk Parker delivered to a small group this fall, and the then-mayoral candidate spoke about how she’s been criticized or attacked, but doesn’t let it bother her. For Bell, it came at a time when “it was just really needed advice.”

She said the burden she has felt to perform is a combination of internal and external pressures.

“I felt like I had to do everything faster, smarter, better than my predecessors who, over 160 years, were all men,” she said. “I had to be very, very thoughtful about everything that I did.”

Parker has talked at times about how she’s turned concerns about her identity, including that she is divorced and coparenting her son, into a positive. During her victory speech Tuesday, she said “experts in D.C.” told her campaign manager “she’s not going to have a chance. She can’t tell people that she’s a single mother.”

In the end, she thought it made her more relatable — and said voters thanked her for bringing her whole self to the campaign trail.

» READ MORE: What Cherelle Parker said about political rivalries, her ex-husband, and charter schools during her victory speech

Joann Bell, head of the Black Women’s Leadership Council, said Parker is uniquely positioned to absorb criticism, given her lengthy career in public service.

“There’s a lot of work to be done, and it won’t be done because we’ve elected one woman. It won’t be done because we’ve elected one Black woman,” she said. “It will be done because we’ve elected somebody who understands how to get a job done, and understands she can’t get it done alone.”

Scranton Mayor Paige Cognetti, a Democrat and the first woman in that role, said the pressures are acute in politics.

“The folks that don’t want you to succeed seem to be more focused on stopping you because you’re the first,” she said. “With anything in politics, there are folks who want to take you out.”

But there are upsides, she said, and some moments of discomfort are easy to turn into tiny triumphs. Cognetti said she often meets with classrooms of children, and at times, a youngster will see her and ask: “Where’s the mayor?”

She’ll respond gleefully, “It’s me!”

“It’s our job to make it normal,” she said. “And when you’re working and working and working all day and night, you’re not focused on it. But when you see in a little girl’s eye in a fifth-grade class, that spark that they see themselves in you, it hits you right in your heart.”

Rawlings-Blake, the ex-Baltimore mayor who now heads the National Basketball Players Association Foundation, said it’s up to women in leadership to press forward in spite of the scrutiny.

“One day, the way people perceive women and Black women will catch up with the reality of our effectiveness,” she said. But until then, “you have to look at yourself at the end of the day and be comfortable with what you were able to do, not necessarily what people say about it.”

Inquirer staff writer Sean Collins Walsh contributed.